(4R,5S)-2,2,4-trimethyl-5-[(1R)-1-phenylmethoxybut-3-enyl]-1,3-dioxolane | 106062-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S)-2,2,4-trimethyl-5-[(1R)-1-phenylmethoxybut-3-enyl]-1,3-dioxolane
• CAS: 106062-14-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: IMMFLPIJMQEWEL-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-2,2,4-trimethyl-5-[(1R)-1-phenylmethoxybut-3-enyl]-1,3-dioxolane 在 18-冠醚-6 氢氧化钾 、 水 、 溶剂黄146 、 乙酰氯 作用下， 反应 10.5h， 生成 methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  寡霉素A的AB二糖单元的全合成

  摘要：

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。

  DOI：

  10.1016/s0040-4039(00)84793-0
• 作为产物：
  描述：

  (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 在 4 A molecular sieve 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (4R,5S)-2,2,4-trimethyl-5-[(1R)-1-phenylmethoxybut-3-enyl]-1,3-dioxolane
  参考文献：
  名称：

  寡霉素A的AB二糖单元的全合成

  摘要：

  描述了一种有效的（10步，总收率17％），高度非对映选择性的二糖全合成，对应于寡霉素A的AB二糖单元。

  DOI：

  10.1016/s0040-4039(00)84793-0

文献信息

• Diisopropyl tartrate modified (E)-γ-[(cyclohexyloxy)dimethylsilyl]- and (E)-γ-(dimethylphenylsilyl)allylboronates: Chiral Reagents for the Enantio- and Diastereoselective synthesis of anti 1,2-diols and 2-butene-1,4-diols via the formal α- and γ-hydroxyallylation of aldehydes
  作者：William R. Roush、Paul T. Grover

  DOI：10.1016/s0040-4020(01)88869-4

  日期：1992.1

  Enantioselective synthesis of 4-substituted (E)-2-butene-1,4-diols and anti 1,2-diols are described. Highly diastereoselective reactions of aldehydes and the chiral PhMe2Si- and (C6H11O)Me2Si- substituted allylboronates 25 and 26 provide anti homoallylic 29 and 50, respectively. Epoxidation of 29 with dimethyl dioxirane followed by acid catalyzed Petersen rearrangement of the intermediate epoxysilanols

  描述了4-取代的（E）-2-丁烯-1,4-二醇和抗1,2-二醇的对映选择性合成。醛与手性PhMe 2 Si-和（C 6 H 11 O）Me 2 Si-取代的烯丙基硼酸酯25和26的高度非对映选择性反应分别提供反均聚物29和50。29用二甲基二环氧乙烷环氧化，然后经酸催化的中间体环氧硅烷醇进行Petersen重排，可得到具有优异对映选择性（81-87％ee）的1,4-丁二醇27。Tamao氧化50提供抗二醇22（ee的64–72％）。这些程序尤其在与一系列氧化的手性醛进行双不对称反应时获得了优异的结果（图1和2）。这些方法有望用于非环状前体糖的非对映选择性合成中。
• A highly stereoselective synthesis of the AB disaccharide unit of olivomycin A
  作者：William R. Roush、Xiaofa Lin、Julie A. Straub

  DOI：10.1021/jo00004a054

  日期：1991.2

  A highly stereoselective synthesis of the AB disaccharide (4c) of olivomycin A is described. The synthesis features the double asymmetric allylboration of alpha,beta-dialkoxy aldehyde 8 using tartrate allylboronate (S,S)-9, which provides triol derivative 10 with the correct relative and absolute stereochemistry for utilization in syntheses of the A and B monosaccharides. The derived diol benzyl ether 11 was converted into 3-hydroxy-2-deoxy-lyxo-pyranoside 16 and thioglycoside 18 via the intermediacy of alpha-methyl 2-deoxy-lyxo-pyranoside 14-alpha, and then 16 and 18 were coupled in CH2Cl2 at 23-degrees-C by using Nicolaou's NBS thioglycosidation procedure to give the alpha,alpha-disaccharide 4a with > 6:1 selectivity. Difficulties encountered in the hydrolysis or activation of the methyl glycoside function of 4a prompted the synthesis to be revised by using intermediates containing more easily deprotected anomeric silyl (TBDMS) ethers. Diol 11 was thus selectivity monosilylated to give 21, which was smoothly converted via 2-deoxy-lyxo-pyranose 23 into thioglycoside 18 and 2-deoxypyranoside 27, which possesses a TBMDS protecting group at the anomeric center. Intermediates 18 and 27 were coupled again by using the Nicolaou methodology in a CH3CN-THF cosolvent mixture at -42-degrees-C to give the AB disaccharide TBDMS acetal 4b with greater-than-or-equal-to 20:1 selectivity. Deprotection of the anomeric TBDMS acetal by using Et3NH+F- in CH3CN then completed the synthesis of the olivomycin AB disaccharide unit 4c.
• ROUSH, WILLIAM R.;LIN, XIAOFA;STRAUB, JULIE A., J. ORG. CHEM., 56,(1991) N, C. 1649-1655
  作者：ROUSH, WILLIAM R.、LIN, XIAOFA、STRAUB, JULIE A.

  DOI：——

  日期：——